Highly Stereospecific, Palladium-Catalyzed Cross-Coupling of Alkenylsilanols

Abstract

[reaction: see text] Alkenylsilanols bearing methyl ((E)-1 and (Z)-1) or isopropyl ((E)-2 and (Z)-2)) substituents are converted to disubstituted alkenes by a palladium(0)-catalyzed cross-coupling reaction with aryl or vinyl iodides in the presence of tetrabutylammonium fluoride or hydroxide. Yields and stereoselectivities are generally high, and the reaction is compatible with a wide range of functional groups.